US6262218B1 - Optical quality polycarbonates with reduced static charge and method for making same - Google Patents
Optical quality polycarbonates with reduced static charge and method for making same Download PDFInfo
- Publication number
- US6262218B1 US6262218B1 US09/450,408 US45040899A US6262218B1 US 6262218 B1 US6262218 B1 US 6262218B1 US 45040899 A US45040899 A US 45040899A US 6262218 B1 US6262218 B1 US 6262218B1
- Authority
- US
- United States
- Prior art keywords
- level
- endcapping
- dihydric phenol
- resin
- diaryl carbonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 24
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 24
- 230000003287 optical effect Effects 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims description 32
- 230000003068 static effect Effects 0.000 title abstract description 27
- -1 diaryl carbonate Chemical compound 0.000 claims abstract description 16
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 16
- 239000000654 additive Substances 0.000 claims abstract description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 16
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical group C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 8
- 229920005668 polycarbonate resin Polymers 0.000 claims description 6
- 239000004431 polycarbonate resin Substances 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical group ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims 8
- 230000000996 additive effect Effects 0.000 claims 4
- 230000000379 polymerizing effect Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 abstract description 8
- 238000009472 formulation Methods 0.000 abstract description 7
- 238000006116 polymerization reaction Methods 0.000 abstract description 6
- 238000000465 moulding Methods 0.000 abstract description 4
- 238000002347 injection Methods 0.000 abstract description 3
- 239000007924 injection Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000428 dust Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000002216 antistatic agent Substances 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000014483 powder concentrate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ITUWQZXQRZLLCR-UHFFFAOYSA-N n,n-dioctadecylhydroxylamine Chemical class CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCCC ITUWQZXQRZLLCR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical class C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
Definitions
- This application relates to optical quality polycarbonates having reduced static charge, and to methods of preparing such materials.
- Polycarbonates have become the material of choice for the manufacture of optical information storage media such as audio disks, digital video disks, laser disks, optical disk memories and magneto-optical disks to which information may be written and from which it may be read from a laser.
- polycarbonates are preferably made by a melt process, such as that disclosed in U.S. Pat. No. 5,606,008, which is incorporated herein by reference. This type of process not only avoids the use of highly toxic phosgene, which is required for manufacture of polycarbonates using the older interfacial (IF) process, it also provides a product with superior optical properties.
- IF interfacial
- One of the challenges facing polycarbonates manufactured using a melt process is the control of static charge, since such static charge can itself interfere with read/write functions and attract a film of dust which also reduces the performance of the optical information storage media prepared with the polycarbonate.
- optical quality polycarbonates are prepared by a method comprising performing a base-catalyzed polymerization of a diaryl carbonate and a dihydric phenol under conditions effective to produce a polycarbonate product having an endcap level of 90% or greater.
- Polycarbonate resins are prepared in a melt process by the reaction of a diaryl carbonate and a dihydric phenol in the presence of a basic catalyst.
- the diaryl carbonate is diphenyl carbonate and the dihydric alcohol is bisphenol A, and these reactants will be used for exemplary purposes throughout the present application.
- Many alternative materials have been proposed for use in preparing polycarbonates, however, and the utilization of such alternative materials is intended to be within the scope of the present invention.
- endcapping reagents are utilized when producing polycarbonates by interfacial processes, rather than melt processes because they can introduce complications to the recovery of various product and recycle streams.
- endcapping generally results from the reaction of the extending polymer with free phenol, which is released as a by-product of the polymerization reaction.
- the endcapping level of a polycarbonate resin can be expressed a percentage value, by determining the number of chains which are terminated with a reactive hydroxyl group (uncapped) and then taking the remainder of the chain ends as being capped. Such a determination can be made using spectroscopic measurements.
- the level of endcapping (E/C%) is then given by the formula:
- Control of the endcap level can be achieved in two ways: (1) by control of the process parameters such that the amount of free diphenylcarbonate in the melt is increased at least during the latter portions of the reaction to increase the frequency of encapping; and (2) by adding a monofunction reagent which will compete with bisphenol A and free diphenylcarbonate to create endcapped polymers.
- the level of endcapping can be increased by increasing the initial ratio of DPC to BPA, and/or by increasing the temperature and/or residence time in the reactor before the polymerization reaction is quenched.
- Preferred conditions have a DPC/BPA ratio of at least 1.05, and preferably 1.07 to 1.137, and a temperature in the last reactor of 286-309° C.
- Residence time can be varied by changing the feed rate of the reactor. The appropriate feed rate will of course vary depending on the size of the reactor. Catalyst concentration and level of vacuum have small effects on the endcap level.
- optical disks produced by the method of the invention may include antistatic additives, stabilizers, including UV and heat stabilizers, and mold release.
- a 10 gallon glass reactor was charged with 2200 g of a 79.9% endcapped melt resin in 16 liters of methylene chloride.
- a typical preparation was as follows: add phenyl chloroformate (13.55 g (0.087 moles),1.0 mole % based on resin) then triethylamine (13.13 g(0.130 moles), 1.5mole % based on resin). This mixture was stirred at room temperature for 30 minutes then washed with successively with 1.0N HCl (10 liters), 0.3N HCl (10 liters) and DI water (4 ⁇ 10liters).
- This resin solution was precipitated into methanol (30 liters) using a 30 gallon henschel mixer. The powder was then dried at 120° C. under vacuum for 12 hours. The resulting powder was extruded using a 30 mm TSE at a rate of 15 lbs/hr with a barrel set temperature of 260° C. This material was molded on a Nessie 160 molding machine preparing 3.5 inch dynatup plaques.
- Formulations were also prepared utilizing a commercial antistatic agent (Atmer 154) and a mold release agent (Glycerol Monostearate). These additives were added to the pellets directly and compounded on a 30 mm TSE at a rate of 30 lbs/hr. Alternatively the additives could be blended into a powder concentrate using a similar melt flow resin with the powder concentrate added as 5% by weight of the total resin volume while compounding, added in a separate feeder. Compact disks were molded on a Netstal Diskjet 600 at a cycle time of 4.43 seconds
- Table 1 summarizes the properties of the materials and the disks produced.
- the static performance was evaluated on dynatups discs by measuring “as-molded” static charge, as well as a qualitative measurement such as dust attraction.
- a 250 liter stirred tank reactor was filled with different ratios of Bisphenol-A and Diphenylcarbonate (0.44 kMol DPC), then purged with nitrogen, and the contents were melted at 140° C. Then 0.00044 mole of sodium hydroxide and 0.11 mole of tetramethylammonium hydroxide were added as a catalyst and stirring was continued for 30 min, after which the temperature was raised to 210° C. and the pressure was lowered to 200 torr. After 30 min the temperature was increased to 240° C. and the pressure gradually lowered to 15 torr.
- Tables 3 and 4 show examples with and without Atmer 154 as an antistatic agent; however we have demonstrated the High EC or High EC+Atmer nations can significantly enhance the antistatic performance for Optical applications.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
TABLE 1 |
Static performance vs % Endcap |
LXOQ Endcapping |
Added PCF | Static (kV)/ | Dust | ||
(mol %) | OH (ppm) | E/C (%) | Stdev | attraction |
none (OQC112) | 827 | 79.5 | −2.50 | (.32) | −− |
0.25 | 554 | 86.6 | −2.15 | (.50) | −− |
0.50 | 404 | 90.2 | −1.84 | (.12) | −− |
0.75 | 243 | 94.3 | −1.35 | (.10) | − |
1.00 | 95 | 97.6 | −1.06 | (.13) | + |
1.25 | 16 | 99.7 | −0.22 | (.18) | ++ |
PCF = Phenyl Chloroformate | |||||
E/C (%) = Molar ratio of phenol endgroups to BPA endgroups | |||||
Static = Surface Voltage (kV units) for “as-molded” dynatups discs - measured using a Meech Static Field meter. Meter-Surface disc distance: d = 5 cm.- Data corresponds to 10 Dynatups samples. |
TABLE 2 | ||
Temp (Last Reactor, | ||
E/C % | DPC/BPA Ratio | ° C.) |
96 | 1.137 | 309 |
90 | 1.073 | 295 |
85 | 1.026 | 286 |
TABLE 3 |
CD-Static performance as a function of % EC and |
Formulation |
CD-Static performance |
Formulation | Atmer | Static (kV)/ | Dust | |
GMS (ppm) | 154 | E/C (%) | Stdev | Attraction |
400 | 0 | 85 | −5.10 | (0.69) | −− |
400 | 250 | 85 | |||
400 | 200 | 90 | −1.70 | (0.69) | ++ |
200 | 200 | 90 | +0.23 | (0.46) | ++ |
400 | 0 | 96 | |||
200 | 200 | 96 | +1.60 | (0.65) | ++ |
400 | 200 | 96 | +0.88 | (0.46) | ++ |
GMS = Glycerol monostereate | |||||
Atmer 154 is the ICI Trademark for POE fatty acid ester | |||||
Static = Surface Voltage (kV units) for “as-moled” Compact Discs - measured using a Meech Static Field meter. Meter-Surface disc distance: d = 2.5 cm.- Data corresponds to 100 CDs samples. |
TABLE 4 |
DVD- Static performance as a function of % EC and Formulation |
DVD-Static performance |
Formulation | Dust | |||
GMS (ppm) | Atmer 154 | E/C (%) | Static (kV)/Stdev | Attraction |
400 | 0 | 85 | −7.59 | (0.40) | −− |
400 | 250 | 85 | −7.13 | (0.54) | −− |
400 | 0 | 96 | −6.20 | (0.36) | − |
400 | 250 | 96 | −3.51 | (0.23) | ++ |
Static = Surface Voltage (kV units) for “as-molded” DVD Discs - measured using a JCI 140C Static Field meter. Meter-Surface disc distance: d = 4.0 cm.- Data corresponds to 100 DVDs samples. |
Claims (20)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/450,408 US6262218B1 (en) | 1999-04-07 | 1999-11-29 | Optical quality polycarbonates with reduced static charge and method for making same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/287,668 US6022943A (en) | 1999-04-07 | 1999-04-07 | Optical quality polycarbonates with reduced static charge and method for making same |
US09/450,408 US6262218B1 (en) | 1999-04-07 | 1999-11-29 | Optical quality polycarbonates with reduced static charge and method for making same |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/287,668 Continuation US6022943A (en) | 1999-04-07 | 1999-04-07 | Optical quality polycarbonates with reduced static charge and method for making same |
Publications (1)
Publication Number | Publication Date |
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US6262218B1 true US6262218B1 (en) | 2001-07-17 |
Family
ID=23103857
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US09/287,668 Expired - Lifetime US6022943A (en) | 1999-04-07 | 1999-04-07 | Optical quality polycarbonates with reduced static charge and method for making same |
US09/450,408 Expired - Lifetime US6262218B1 (en) | 1999-04-07 | 1999-11-29 | Optical quality polycarbonates with reduced static charge and method for making same |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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US09/287,668 Expired - Lifetime US6022943A (en) | 1999-04-07 | 1999-04-07 | Optical quality polycarbonates with reduced static charge and method for making same |
Country Status (10)
Country | Link |
---|---|
US (2) | US6022943A (en) |
EP (1) | EP1171505B1 (en) |
JP (1) | JP3864053B2 (en) |
KR (1) | KR100708500B1 (en) |
CN (1) | CN1229417C (en) |
AT (1) | ATE298772T1 (en) |
BR (1) | BR0009598A (en) |
DE (1) | DE60021067T2 (en) |
TW (1) | TWI229101B (en) |
WO (1) | WO2000059984A1 (en) |
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US20090117314A1 (en) * | 2007-11-07 | 2009-05-07 | Bayer Materialscience Ag | Process for the preparation of polycarbonate by the melt transesterification method |
US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
WO2014044823A1 (en) | 2012-09-20 | 2014-03-27 | Ovizio Imaging Systems NV/SA | Digital holographic microscope with fluid systems |
US10106648B2 (en) | 2014-11-19 | 2018-10-23 | Sabic Global Technologies B.V. | Method of polymerizing end-capped polycarbonate and end-capped polycarbonates derived therefrom |
EP3196631A1 (en) | 2016-01-19 | 2017-07-26 | Ovizio Imaging Systems NV/SA | Digital holographic microscope with electro-fluidic system, said electro-fluidic system and methods of use |
US11879035B2 (en) | 2018-10-11 | 2024-01-23 | Sabic Global Technologies B.V. | Polycarbonate |
US12077635B2 (en) | 2018-10-11 | 2024-09-03 | Sabic Global Technologies B.V. | Method for the manufacture of polycarbonate |
Also Published As
Publication number | Publication date |
---|---|
JP2002541284A (en) | 2002-12-03 |
ATE298772T1 (en) | 2005-07-15 |
JP3864053B2 (en) | 2006-12-27 |
KR20010102582A (en) | 2001-11-15 |
CN1229417C (en) | 2005-11-30 |
DE60021067T2 (en) | 2006-05-18 |
KR100708500B1 (en) | 2007-04-16 |
US6022943A (en) | 2000-02-08 |
CN1345348A (en) | 2002-04-17 |
DE60021067D1 (en) | 2005-08-04 |
EP1171505A1 (en) | 2002-01-16 |
EP1171505B1 (en) | 2005-06-29 |
TWI229101B (en) | 2005-03-11 |
BR0009598A (en) | 2002-01-02 |
WO2000059984A1 (en) | 2000-10-12 |
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